About Us

Boating Excursions and Overnight Stays

Come enjoy the water with Captain Chester Ruder on a 38 foot Catamaran or our 43 foot yacht. We offer sailing trips, snorkeling and kayaking, dinghy drinking tours of waterfront bars (you can call it an "eco-tour" if you prefer), overnight stays through Airbnb, overnight excursions and lobstering in season.

Where we are

We are located 5 miles from the famous Duval Street in Key West. Our boats are docked immediately behind the Hogfish Bar and Grill on Stock Island, one bridge away from downtown Key West. We have Free Parking.

400 Great Reviews on Airbnb

Stray Cat Sailing Adventures has been in business for more than 10 years. Captain Ruder is licensed through the US Coast Guard and holds a 100 ton Masters license with all Sailing Endorsements. Captain Ruder has more than 400 great reviews on Airbnb.

Spend the Night on a Sailboat

CAll us at 361-416-0054

We'd love to help you plan a great adventure

Stray Cat Sailing Adventures

6810 Front St, Key West, FL 33040

(361) 416-0054